Thesis- The sloppily dressed, wealthy businessman, who now has the state-of-the-art mansion, but because of his penny pinching ways, no one would ever know it.
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Granted Oliver Toliver wasn’t a very well dressed young man growing up; however after achieving the wealth he has today, you would think he would invest in a better wardrobe. The plaided flannel shirt with the denim blue jeans are not typical business attire. The jeans have worn spots on them and could use a good cleaning, as well as the flannel shirt having several bleach spots on it, and a slight odor. His gruffy looking face with disheveled, unkept hair makes him look more like a lumberjack than a businessman. But for some reason he has remained true to himself and has not change who he is as a person to please other people’s beliefs on what he should wear.
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Eventually after his continued hard work and perseverance he was able to build a state-of-the-art mansion with every up to date gadget possible. When entering the road towards the mansion, the drive is lined with a very unique lighting system the entire way. In order to get to the doors of the mansion, everyone is met at the gate by a guard, who checks a computerized screen for your name. Finally, reaching the front door, the guest is greeted by Oliver, who begins to give a tour of his home. There is nothing that can compare to anything they have ever seen or heard before, with one remote controlling most of these incredible gadgets. Wow!
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Penny-pinching is what some people do to save money, but for Oliver it is his only way, and it has made him very successful because of it. By looking at him, you would never guess that he is extremely wealthy, but because he has done this from such a young age, it is the only thing he knows how to do. He did however splurge with the construction of his mansion and give it all those fancy gadgets. But even after spending the money to build the mansion, he still did not change his miserly ways with updating his wardrobe to more of a business attire. Oliver will go to his grave a frugal, tight fisted and cheap man to maintain the true person that he is and will always be remembered as.

Please go over your paper with the following in mind. Thanks to PsyDAG for the following:

In the future, if nobody is available to proofread your work, you can do this yourself. After writing your material, put it aside for a day — at least several hours. (This breaks mental sets you might have that keep you from noticing problems.) Then read it aloud as if you were reading someone else's work. (Reading aloud slows down your reading, so you are less likely to skip over problems.)

[You can also either read it aloud to someone else or have someone else read it aloud to you! (The latter works really well!)]

If your reading goes smoothly, that is fine. However, wherever you "stumble" in your reading, other people are likely to have a problem in reading your material. Those "stumbles" indicate areas that need revising.

Once you have made your revisions, repeat the process above. Good papers often require many drafts.

The sloppily dressed wealthy businessman Oliver Toliver, had the state-of-the-art mansion, but because of his penny-pinching ways, no one would ever know it. Whoever thought the introverted boy, with the funny name would turn out to be so prosperous and well off. He has stayed true to himself, never allowing anyone to waiver his beliefs, even after achieving such wealth. The smile you see displayed across his face is one of determination, hard work, and true satisfaction of what it took for him to become successful. Many times Oliver Toliver questioned “Why” his parents would name him such a name, now he knew, it was a name that most people would never forget.

No one would ever have known that this sloppily dressed, wealthy businessman, with his penny-pinching ways, would have built a state-of-the-art mansion. Whoever thought the introverted boy, with the funny name would turn out to be so prosperous and well off. He has stayed true to himself, never allowing anyone to waiver his beliefs, even after achieving such wealth. The smile you see displayed across his face is one of determination, hard work, and true satisfaction of what it took for him to become successful. Many times Oliver Toliver questioned “Why” his parents would name him such a name, now he knew, it was a name that most people would never forget.

In the conclusion, I'd reword the first sentence so it's not such a repeat of the thesis statement. It needs to convey the same ideas, but not the identical words. The rest looks good except for these things:

No one would ever have known the sloppily dressed, penny pinching Oliver Toliver, was now the wealthy businessman with an incredible state-of-the-art mansion. Whoever thought the introverted boy, with the funny name would turn out to be so prosperous and well off. Even after achieving such wealth, Oliver has always remained true to himself, he never allowed his beliefs to waver. The smile you see displayed across his face is one of determination, hard work, and true satisfaction of what it took for him to become successful. For many years Oliver Toliver questioned why his parents would name him such a name, now he understood, because it was a name that most people would never forget.